


Really, you should have seen this one coming

by thatoldeblackmagic



Category: Critical Role (Web Series)
Genre: F/M, Fluff, Getting Together, No angst zone, couples that prank together stay together, even tho caleb tries, fake dating for the con
Language: English
Status: Completed
Published: 2019-04-04
Updated: 2019-04-04
Packaged: 2020-01-04 16:00:32
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,402
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18346955
Author URL: https://archiveofourown.org/users/thatoldeblackmagic/pseuds/thatoldeblackmagic
Summary: The book shop that Jester finds herself in with Caleb is one of the most stuffy and pretentious places she’s ever been in her whole life which is saying a lot since she visited the Cobalt Soul library with Beau that one time.It’s the kind of place where you feel like you have to whisper, where if you breathe too loud or walk to quickly you’ll get kicked out, and Jester can feel her blood thrumming beneath her skin.  She wants to fuck the whole place up.The only thing is that her partner in crime is not paying attention.  At all.





	Really, you should have seen this one coming

The book shop that Jester finds herself in with Caleb is one of the most stuffy and pretentious places she’s ever been in her whole life which is saying a lot since she visited the Cobalt Soul library with Beau that one time.

It’s the kind of place where you feel like you have to whisper, where if you breathe too loud or walk to quickly you’ll get kicked out, and Jester can feel her blood thrumming beneath her skin. She wants to fuck the whole place up.

She wants to rearrange the books by color to form a giant rainbow, she wants to paint swirling patterns on the clean, crisp, mahogany bookshelves, the boring off-white walls, the stark tile floor. She wants to scream and sing and dance and introduce life into this dull place.

She wants so badly, and it must show, because the prim and proper gnomish woman at the front desk won’t. stop. looking at her.

The woman read the both of them as they entered the store, her eyes scanning over Caleb briefly and clinically, presumably finding him acceptable, before moving on to Jester where they just sort of fixated. Her overly-large golden brown eyes are absolutely locked onto Jester, have been for the whole 20 minutes they’ve been in this store, and it’s honestly not helping with Jester’s whole thing right now. It’s more exciting this way. It's forbidden fruit dangling right out in the open over a bear trap covered in wasps. The reward will be that much more satisfying if she can only fucking get to it.

The only thing is that her partner in crime is not paying attention. At all.

Caleb walked into the store and immediately reached nirvana.

His steps had slowed as he crossed the store threshold, walking with quiet care to not disturb the atmosphere. Jester watched as he continued forward between two of the shelves and reached out his left hand to let his fingertips lightly drag over the spines of the books. She’s sure he wasn’t even looking at the titles yet, just taking in the entirety of this place, all its potential knowledge, the crisp clean smell of parchment and ink. 

He walked right past the front desk. He probably didn’t even register that anyone was there.

From then on he was lost to her, totally engrossed in the action of picking up a book, flipping through some pages, carefully placing it back, then picking up the next book in sequence. Rinse, and repeat for 20 more minutes or something.

Jester found her own book relatively quickly, another cookbook for Deucey focusing on pastries this time (because Jester can hope), then spent the next 15 minutes pretending to be scholarly and smart and flip through books without really seeing any of the words.

She only managed to turn one book upside down when the shopkeeper had to sneeze.

Picking up books and putting them down can only keep Jester occupied for so long (15 minutes), and now she’s just fucking bored. Her mischief in this shop has been kept to its minimum and she’s ready to either leave, or just say fuck the whole thing and start painting on the walls anyway.

The only downside is that Caleb probably wouldn’t get his books if she gets them both kicked out. 

He has finally moved into another aisle with two books tucked under his arm, now engaged in a balancing act as he continues to look through books with only one free hand. 

And naturally, with the store momentarily unavailable to her, Jester focuses on a new target.

“Cayyleb,” Jester sing-songs as she skips over to him, placing herself between him and the woman at the desk. He doesn’t even look up as she presses herself along his side, angling so she can hook her chin over his right shoulder, doesn’t even acknowledge Jester looping her arm into his and slipping her own book in between the two he carries. 

Well, she figured it wouldn’t be that easy, and it wouldn’t be any fun if it was. “What are you reeadding?” She drawls purposefully too loud against the quiet of the store. 

His eyes flick over toward her, briefly meeting her own, before turning back forward. “A book,” Caleb responds at whisper level. 

“What kind of book? Is it about magic? Are you going to buy it?”

Caleb lets out a sigh heavy enough to she can feel it move through his chest as he finally turns his head to better see Jester. Their faces are close like this with her head still resting on his shoulder, and Jester gets an absurdly strong impulse to stick out her tongue and see if it will reach his cheek.

She gives in. 

It does.

The recoil from Caleb’s full body flinch manages to shakes Jester off from her perch on his shoulder, but she still has a firm hold around his arm. She uses it like a tether to pull him back in, repositioning herself against his side, and she briefly realizes how strange it is that he doesn’t resist at all.

With a snap, Caleb single-handedly closes the book in this left hand and slowly, purposefully slides it back onto the shelf, letting his index finger drag down the spine, which is weirdly hot if Jester thinks too much about it.

Luckily she doesn’t have to because Caleb’s now free hand raises up to pinch her nose, not hard but not soft either, as he says, “I can only afford two books. What do you want.”

Jester smiles and takes advantage of the situation by pushing her tongue out again, this time pressing it against Caleb’s left palm as it hovers in front of her face. He doesn’t flinch back this time, but he does quickly let go of her nose, wiping his hand on her dress before returning it to his side. “I’m so booooored,” Jester replies. “The woman at the desk keeps watching me, like she’s expecting me to draw in all the books or something!” She’s listening now too, shamelessly without even the illusion of privacy.

“You would never,” Caleb says with a barely audible smile. Jester can’t see it at the moment, but she imagines that it’s small, maybe just the slightest quirk of the corner of his mouth. 

Then he turns his head a bit to angle down toward her neck so that his mouth is hidden from view behind her hair. He leans in slightly and Jester feels her grin turn wicked when she realizes what this must look like to that woman. When he speaks again, his voice is lower, and even as close as Jester is, she can barely hear him say, “Give me another 15 or so minutes and I will help you. I am just about done in here.”

His breath tickles the shell of her ear and Jester feels a light buzzing behind her sternum. “You’re right,” Jester replies, rocking back onto her heels and detangling herself from Caleb. “I would never ever do that, even if you begged me to.”

Caleb tilts his head down and maybe possibly rolls his eyes which Jester is absolutely sure he picked up from Beau.

With quick kiss blown over her shoulder, Jester spins on her heel and proceeds to spend her 15 minutes weaving through the aisles and sussing out any blind spots that she can work to her advantage. The thing is, this place isn’t very big. There are no nooks or hidey-holes in between shelves, and the checkout counter is right at the front of the store facing the back wall which gives the woman a full line of sight down each of the four aisles.

It’s all up to Caleb then. Jester only hopes that he buys the books first and distracts second so at least he can keep them if they do get kicked out.

And then, after what she assumes is 15 minutes to the second, Jester hears Caleb’s footsteps thud against the hard tile floor, not loud by any means, but far louder than he has been since they stepped foot through the door. She slows her steps and turns behind the rear edge of a bookshelf to obscure herself as much as possible.

“Hallo,” Jester hears from the front of the store followed by the soft ‘thwump’ of the books hitting the wooden counter. “Your collection is well chosen and I believe I could spend all day in here given the opportunity, though for today I have whittled my selection down to these three.”

Slowly, Jester edges around the corner, peeking her head barely around the side so she can just see Caleb completely blocking the view of her current aisle. She blows another kiss to Caleb's back for good measure, and then Jester gets to work.

She’s listening as she moves, flipping and rearranging books a she catches snippets of conversation.

It’s all general bookish small talk with Caleb doling out the charm that Jester sometimes forgets he possesses. ‘Ah, yes. I’m quite proud of all of my books’, ‘I noticed a large amount of whatever, are you interested in smart people shit?’, ‘Ah!!! Yes!!! I’m the smartest person of them all!!!!’ Or something like that. Jester catches about half of the words because the woman’s voice is a bit quieter than Caleb’s and nothing they’re saying is very interesting, until Jester manages to catch the tail end of a sentence, “...buy a cookbook?” It sounds confused, a change of pace from their banter which manages to get Jester’s attention.

“It’s a bit incongruous.” The woman continues as Jester strains to listen.

“Ah, I suppose so,” Caleb replies. Jester turns to look up front and catches Caleb leaning in, resting his elbows on the front counter. Then, of all things, he stage whispers to the woman, “You see, pastries are her favorite.” 

And with that, Jester hastily shoves the charcoal she was doodling with back into her pocket and pretends to flip through the random book she had grabbed. Just in time too, as the shopkeeper cranes around Caleb to peek over right at Jester. 

After a second, the woman moves back, placing her own elbows on the counter and leaning forward as if her and Caleb are sharing a secret. She says softly, almost too soft for Jester to hear, “Oh, now I do see. Is this for a special occasion, or just because?”

“No, no, nothing special. Just a pleasant surprise if I don’t manage to completely screw up the recipe.” Jester moves again, carefully setting the book horizontally over the top edges of the highest row she can reach.

“Here’s a tip from me to you” The woman says in a voice more kind than Jester would have imagined. “It never hurts to go heavy on the sugar, and always use butter instead of lard. It’s worse for you, but tastes much better.”

Jester watches as Caleb nods and moves back from the center of the desk to stand at his full height. “I appreciate your advice, gods know I need it. Ah, forgive me, I failed to ask, how much for all three?”

“Forty gold.” She says primly, and holy shit that is absurd. Forty gold for three whole books is basically the same as robbing a person blind and kicking them in the shin on your way out. 

Jester turns over, about to step in just as Caleb says, “Ja, alright” And pulls out his coin purse. “One,” clunk. “Two,” clunk. Three,” clunk.

It takes all Jester has not to laugh out loud. She gets its, finally, that this whole gag was only partially about saving a gold or two, but mostly it gives Nott all the time she needs to snag any trinket that caught her eye.

The woman’s attention is fixated on the individual gold carefully placed on the counter, and Jester breaks loose. Around ‘six’ she pulls out her paints and finishes a semi-proportional dick on the rear edge of the shelf buy ‘ten’. By ‘twelve’ she moves to the next aisle, deftly switching books, flipping them upside down, hastily drawing the Traveler’s symbol on the front cover of a couple. By ‘twenty-five’ she has a few books tucked in her arms, scurrying to the furthest aisle to stash them wherever they fit, pulling more from those shelves to be relocated as well. 

It’s at ‘thirty-seven’ that Caleb stops. Well, what would be ‘thirty-seven’ if he hadn’t skipped ‘fifteen’ and ‘twenty-eight’. “Ah,” He says as if vaguely surprised. “Forgive me, it appears I miscalculated. This is… embarrassing. It’s um, well.” He breathes in deep, “I’m afraid I must put this back.”

Jester immediately stops what she’s doing, and peers over to where Caleb is holding up her cookbook. It’s fortunate enough he said it loud enough that she would hear, because the gnome woman glances over at her before leaning back in to quickly fumble through the gold laid out on the table.

Apparently she doesn’t fumble well enough to notice the missing two, because she says with a full voice, “We’re actually having a sale today. That one in particular is included, which brings your total to thirty-seven gold.”

Caleb visibly pauses, stilling himself before leaning forward as well. “You are being very generous with that, and I, well. If it is not too much to ask, I would like to take advantage of that sale.”

“Done” She says, sweeping the thirty-five gold into a small pouch without a second word. “I hope it goes well.”

The books are already tucked under Caleb’s arm as he says, “As do I. Again, thank you for the advice.” He turns to Jester and slightly lifts a brow, speaking louder now to get her attention, “Liebling, are you ready?”

“Readyyyyy!” Jester says, hastily stuffing one last book wherever she can before skipping over and hooking her arm into Caleb’s. She turns to the woman whose focus is back onto Jester now, though its softer, not as intense. “Have a nice day, thank you so much!”

Jester lets the door shut behind them. Immediately, she turns to Caleb and says, “Sooooo when is our anniversary? Can it be in the winter when all the leaves are crispy and like you can see your breath in the air?”

“I was hoping for summer actually. Maybe with some lightning bugs in the background on a night when it is not so hot.” He replies without a pause. And he’s doing that thing again, that face she recognizes now where his mouth is still, but his eyes are shining, one eyebrow slightly raised.

He’s amused, he’s playing into her whims, so she says, “Does that mean our first date was outside? Like on a picnic? But wait, lightning bugs only come out at night. Oh! I know! We went stargazing!” Jester reaches down and threads her fingers through his, bringing their hands up as she points toward the sky. “I showed you all the constellations I know just like this, but you weren’t paying attention at all. You just stared at the side of my face the whole time.”

She turns toward him with a grin and realizes she predicted correctly, he is looking at her now eyes still bright, and a small smile pushing at the corner of his mouth. Slowly, Jester lets their hands drop back between them, but she doesn’t let go. And somehow neither does Caleb.

So they stay like that, walking hand in hand, and the buzzing behind Jester’s sternum spreads outward through her chest, settling somewhere high in her stomach. She can’t help but smile as she says, “What if we called it ‘rooty-tooty’?”

“Oh, you want to make this an official con? One for the books?” Caleb replies with one eyebrow raised. Like this, when he’s barely ginning and playing coy, he looks almost like the man Jester used to daydream about meeting in her travels, the charlatan with the wolfish grin, a hustler that only had eyes for her. Almost, not quite, but Jester finds she like this even better. 

“Yeah! Why not? You and Nott have like a whole bunch together, we should have one too!”

“Then tell me, what are the practical uses of ‘rooty-tooty’?”

“Welllll, what if there is a couple’s discount on incense or paper or books?” Jester swings their arms in a wide arc as she thinks. “Or what if like today a shopkeeper won't stop looking at me because she thinks I’m going to steal something or whatever, then you distract them so I can paint a dick on the wall!”

He turns to her now, his face a mixture of apparent disbelief and subtle happiness, “You had time to paint a dick on the wall?”

“Well technically, not on the wall. Just the back of one of the bookshelves.”

Caleb huffs out a laugh at that, more a short exhale than anything, but Jester still thinks it counts. “She was not watching to see if you would steal something. I think she was unfamiliar with someone as vibrant as you are waltzing into her quiet little shop. I very much doubt she gets more than a few customers per day, and most of them probably look more like me.”

“Maybe a little less scruffy though.” Jester says as she lifts her free hand up to poke at Caleb’s cheek. And again, he doesn’t react, doesn’t pull away or swat at her hand. He’s been letting her get away with a lot today and it only makes Jester want to keep pushing, to see how far he’ll let her go. 

So, of course, Jester does. She moves her finger back across his cheek, catching it in his hair and tucking some strands carefully behind his ear. Using her nail this time, she drags a line down behind the shell of his ear to his jaw, then continues a slow path down the line of his neck all the way to where his collar obscures the rest.

The reaction is almost instantaneous. It’s literally the most satisfying thing right now for Jester to watch a splotchy flush appear high on his cheeks.

He isn’t looking at her now, his face pointedly turned forward, and Jester wonders if he will look at her again if she asks. 

“Caleb,” Jester says as she pivots herself to face him and takes his other hand in her own. They’ve stopped walking now, standing along the side of the street, and Caleb is looking absently over her left shoulder still refusing to meet her eye. “Caleb, will you look at me?”

And then miracle of all miracles, he does.

His mouth is pulled into a tight line, but his eyes are soft as they meet hers. The blush has extended to his hairline now, and it makes his early summer freckles stand out even more.

Jester wants to push further. She knows how she feels about Caleb, has known for a while now. She figured it out one night months ago when he made her laugh so hard that milk came out of her nose and instead of getting embarrassed, it just made her laugh even harder. 

It’s just that their relationship is solid as it is, the foundation firm and steady, and Jester hadn’t wanted to break something so good. They’re family now and they both had to work hard to get to this point, and it’s not that Jester isn’t happy with how they are. She is, extremely so, but it’s moments like these when she thinks she can see something behind his eyes, something he’s been hiding and trying to deny himself for a while, that makes Jester want to test the boundaries.

“We should go stargazing sometime,” Jester says softly. She watches Caleb’s eyes widen just barely, his mouth tighten around the corners, “I knows it’s just barely summer, but I think it’s warm enough that we could find some lightning bugs if we really tried. I know a lot of constellations, and I can show you every single one if you’ll let me.”

Caleb stares at her flatly for almost five full seconds before he attempts to respond, his mouth opening then snapping shut again as he finds the words to say. “Jester. What is... what are- Scheisse.” He pauses to gather his thoughts once more, and she can feel his hands fidgeting within her own, his fingers flexing out then curling back over her palms. Then, finally, he says “Is this about our con?”

“Well, kind of? I mean, I started to think like, what if it wasn’t a con, you know? Or at least that part of it. We could still distract shopkeepers and swindle out a few gold and keep calling it ‘rooty-tooty’ because that’s a really good name, but the set up can be real at least.” Jester says, or rambles really. 

She knows that she talks too quickly sometimes when she just needs to get something out, and she knows she left out an important bit which is why she follows up with a hastily added, “Only if you want to though. If you don’t that's totally fine too and I won’t be like upset or heartbroken or anything like that, I promise.” She can feel her confidence from earlier evaporate into thin air as she keeps rambling and proceeds to make a promise she doesn’t know if she can keep.

Caleb is looking at her know like he has no idea what to make of her. Or maybe Jester just doesn’t know what to make of his expression. “Do you want to?” He replies, which is a silly thing to ask.

“Well yeah, that’s why I said it!” Jester tries to smile, but she can feel that it’s brittle behind all her nerves. She end up squeezing Caleb’s hands in hers and says, “But like really whatever you want I am okay with. I won’t be hurt or sad or-”

“Jester,” Caleb says firmly as he cuts her off. The blush has pushed past his face and extends down the sides of his neck which is almost too fucking cute for Jester to handle. “I- I do want to. Just, I do not think-”

“Hold it right there mister.” Jester interrupts this time, letting go of one of Caleb’s hands to lift up her own in the universal ‘halt’ motion. “If what you’re about to say next is sad or self deprecating or something silly like ‘Oh, what about Fjord?’, just know that I will not be having it.”

Her words clearly throw Caleb for a loop as his face cycles between surprise, frustration, then eventually settles into an adorable pout.

His lips are pursed and tilted in the slightest downward angle and Jester knows she’s going to draw this in her journal later because its just so dang cute. “But Jester,” He starts again, “You know me. You know those things I am apparently not allowed to talk about do have weight and should be taken into consideration.”

“And you know me. Or at least you should know me well enough to figure out that I already thought about all that stuff, like forever ago, and decided that I still like you a lot.” And there, she said it. Hopefully spelling it out like that will be enough for Caleb to come to terms with the fact that he can’t scare her away no matter how hard he keeps trying.

Jester drops her upraised hand back to Caleb’s and re-laces their finger together. She’s smiling for real now, so wide it makes her nose scrunch up. “Plus I can’t let you bail on our first date before you even agree to go.”

Caleb exhales like he was punched in the gut. “Jester…” He says, more breath than voice.

“Cayylebbb,” Jester sings back, tightly squeezing his hands in her own.

He’s searching her face now, looking for… well several things probably. Doubt, hesitation, pity, any sign that Jester is going to say “What a funny joke!” or something dumb like that. It’s good that all Jester is feeling right now is a bubbly sort of joy that pops like champagne bubbles in her chest and makes her want to float up into the sky. 

“We passed a lake on the way here,” Caleb says eventually, softly. “It is just outside of town, within walking distance if I am not mistaken. I am just mentioning this because lighting bugs are often found around bodies of water.”

“Let’s go tonight!” Jester blurts out excitedly. She can’t really help it though, she feels almost like she’s vibrating with energy, with light and warmth and a restlessness that has her bouncing on the balls of her feet. “We can bring a blanket and maybe snacks and we can walk there through the sunset, then by the time we get there maybe the lightning bugs will be out!”

There's a beat where Caleb just looks at her, openly, searchingly, and then he caves. Caleb laughs for real, its breathy and comes from somewhere deep within his chest and all Jester wants to do is press her ear to his sternum and listen. She doesn't get the chance to, though hopefully she will in the future, because he says, "That sounds wonderful. I would like to. Do that I mean. Go on a date."

And she can tell he's about to kick himself for his stilted speech, but to be fair Jester is about at that same level. Which is why instead of saying anything at all, she leans in and presses a firm kiss to dimple on his left cheek. 

The heat on his face is tangible now, and her pursed lips curve against his face into a smile.

Jester pulls back, still grinning and adjusts herself to stand back at Caleb's side, swinging their arms together between them. "Let's go back to the inn and woo the cook into letting us use the kitchen because I totally want to make really good snacks for our date."

Caleb faces forward, his mouth pulled down in exaggerated severity as he nods, not saying anything, and squeezes her hand tightly in his own.

And Jester laughs, leaning in to press another kiss to his temple, one along his jaw, before pulling him forward by their joined hands.

**Author's Note:**

> widojest because i guess this is who I am now
> 
> I wrote 3000 words of this in a fever state then struggled to make the rest like a week later. anywayy writing this got me through the 2 week anticipation of what the hell happens next with the m9 and i hope you like it!!


End file.
